About: Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums

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About: Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Trisubstituted piperazinones, piperazines, tetrahydropyrazines, and dihydropyrazinones were prepared in a one-step procedure from easily accessible polymer-supported acyclic precursors containing either a masked aldehyde or ketone group. Acid-mediated unmasking of the aldehyde triggered cyclic iminium formation followed by reduction with triethylsilane present in the cleavage cocktail. The effect of the substituent at the iminium-forming nitrogen was evaluated: whereas complete conversion to the target compounds was observed with N-alkyl, aryl, and phenylsulfonamido derivatives, the N-acyl compound suffered from a partial reduction of the aldehyde to an alcohol. Similarly, ketones readily provided cyclic iminiums with N-alkyl compounds, whereas their cyclization with N-acyl precursors proceeded unwillingly. Interestingly, cleavage of the resin-bound acyclic precursor at 60 °C in the presence of triethylsilane resulted in the decomposition of the amide bond and formation of a lactone. An analogous synthetic route was also successfully used for the preparation of piperazines and tested as an alternative route for the synthesis of diazepanones. Trisubstituted piperazinones, piperazines, tetrahydropyrazines, and dihydropyrazinones were prepared in a one-step procedure from easily accessible polymer-supported acyclic precursors containing either a masked aldehyde or ketone group. Acid-mediated unmasking of the aldehyde triggered cyclic iminium formation followed by reduction with triethylsilane present in the cleavage cocktail. The effect of the substituent at the iminium-forming nitrogen was evaluated: whereas complete conversion to the target compounds was observed with N-alkyl, aryl, and phenylsulfonamido derivatives, the N-acyl compound suffered from a partial reduction of the aldehyde to an alcohol. Similarly, ketones readily provided cyclic iminiums with N-alkyl compounds, whereas their cyclization with N-acyl precursors proceeded unwillingly. Interestingly, cleavage of the resin-bound acyclic precursor at 60 °C in the presence of triethylsilane resulted in the decomposition of the amide bond and formation of a lactone. An analogous synthetic route was also successfully used for the preparation of piperazines and tested as an alternative route for the synthesis of diazepanones. (en)
Title	Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums (en)
skos:prefLabel	Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums (en)
skos:notation	RIV/61989592:15310/12:33141476!RIV13-MSM-15310___
http://linked.open...avai/riv/aktivita	P
http://linked.open...avai/riv/aktivity	P(ME09057)
http://linked.open...iv/cisloPeriodika	26
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Vaňková, Barbora Krchňák, Viktor Brulíková, Lucie
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Palackého v Olomouci / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	172981
http://linked.open...ai/riv/idVysledku	RIV/61989592:15310/12:33141476
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Piperazinones, Cyclization, Piperazines, Solid-phase synthesis, Iminiums, Heterocycles (en)
http://linked.open.../riv/klicoveSlovo	Heterocycles Solid-phase synthesis Cyclization Iminiums Piperazines Piperazinones
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[EDBAD6B3CF6B]
http://linked.open...i/riv/nazevZdroje	European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...vavai/riv/projekt	Research of new organic compounds with anticancer activity with use of combinatorial chemistry
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	N
http://linked.open...iv/tvurceVysledku	Krchňák, Viktor Vaňková, Barbora Brulíková, Lucie Wu, Boyuan
http://linked.open...ain/vavai/riv/wos	000308294700026
issn	1434-193X
number of pages	10 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/ejoc.201200591
http://localhost/t...ganizacniJednotka	15310

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